Total Synthesis of Luminmycin A, a Cryptic Natural Product from Photorhabdus Luminescens

Abstract

Luminmycin A, a natural proteasome inhibitor transcripted by a silent gene cluster from Photorhabdus luminescens, belongs to the compound family of the syrbactins and is structurally closely related to the glidobactins. Key step for the synthesis of the 12‐membered cyclopeptide ring is an intramolecular Horner–Wadsworth–Emmons reaction, while the double unsaturated fatty acid side chain can be obtained via phosphane‐catalyzed isomerization of a corresponding acetylenic fatty acid ester.